Demo

Senior Director, Digital Workplace Experience

Dale WorkForce Solutions
Chicago, IL Full Time
POSTED ON 12/17/2025
AVAILABLE BEFORE 1/17/2026
Responsible for leading the development and implementation of the digital workplace strategy.

This is a strategic leadership role with a mission: to delight users, drive adoption, and create a digital environment where technology is an enabler—not a barrier—to success. Oversee budget of up to $20M. Oversee the integration and optimization of collaboration tools (e.g., Microsoft 365, Teams, SharePoint), endpoint management, audio video solutions, and digital assistant technologies. Stay ahead of emerging trends in digital employee experience, workplace automation, and AI-driven productivity tools. Team size 15 plus external partners.

The role focuses on enhancing employee productivity, collaboration, and user experience through the effective use of technology across on-premise, cloud, and SaaS environments. The individual in this role will oversee the design and delivery of integrated digital solutions that support a dynamic, hybrid work environment. This includes ensuring secure, seamless, and resilient technology experiences for all employees. The position requires close collaboration with functional leaders to develop and maintain digital experience roadmaps that address current organizational needs and incorporate emerging technologies. As a strategic leadership role, this position is accountable for driving user adoption, improving digital engagement, and ensuring that technology serves as a key enabler of organizational success.

  • Technology Innovation:
    • Oversee the integration and optimization of collaboration tools, endpoint management, audio video solutions, and digital assistant technologies.
    • Stay ahead of emerging trends in digital employee experience, workplace automation, and AI-driven productivity tools.
  • Strategic Leadership:
    • Define and drive the digital workplace vision, roadmap, and KPIs to support a hybrid, digitally native workforce.
  • In-office / Hybrid Experience:
    • Create and maintain technology solutions that deliver seamless and convenient services during in-person and remote collaboration.
    • Ensure in-office AV technologies are reliable and dependable.
    • Provide a modern workplace experience.
    • Identify ways to simplify the integration of physical and technology environments.
    • Support hybrid work arrangements.
  • Strategic Communicator:
    • Lead and shape strategic communications that emphasize the role of digital experience management through value-based storytelling to foster a digitally savvy workforce.
  • Change Management:
    • Lead enterprise-wide adoption strategies, training, and communications to ensure successful rollouts and sustained use of digital workplace solutions.
    • Ensure usability and adoption of technological solutions for all teammates.
  • Cross-Functional Collaboration:
    • Partner with HR, Facilities, Security, and Information technology teams to align digital workplace initiatives with the employee lifecycle in a frictionless manner.
  • Security & Reliability:
    • Ensure all digital workplace solutions meet security requirements and are delivered with an emphasis on continuously improving the digital workplace to delight our customers.
  • People Leadership:
    • Drive effective performance management, fostering professional growth, and creating a positive and inclusive work environment.
    • Utilizes proficient leadership and communication skills to motivate and inspire team members, ensuring they are aligned with and committed to achieving the organization's goals.
Qualifications

  • Education
    • Preferred Bachelor's Degree; or equivalent experience
    • 12 Years of progressive leadership experience in Information technology, digital transformation, or workplace technology. Required
  • Knowledge Skills and Abilities
    • Track Record in delivering enterprise-scale digital workplace programs with a proficient focus on end-to-end user experience.
    • Deep understanding of employee experience platforms, collaboration ecosystems, modern technology deployment models, and endpoint technologies.
    • Strategic Leadership: Ability to lead strategic initiatives with a clear vision and measurable outcomes that motivate and inspire cross-functional teams.
    • Stakeholder Engagement: Proficient stakeholder management skills with the ability to influence and build consensus at all levels of the organization.
    • Communication and Presentation: Excellent oral and written communication skills, including the ability to negotiate, persuade, and deliver effective presentations to diverse internal and external audiences.
    • Executive Presence and Integrity: High level of poise, integrity, and professionalism, with a can-do attitude and proficient critical thinking skills.
    • Demonstrated executive presence in interactions with senior leadership. Relationship Building: Exceptional interpersonal skills for building and maintaining key relationships across the organization and with external partners.
    • Ability to represent the organization effectively in various forums. Decision-Making and Results Orientation: Demonstrated ability to establish credibility through sound decision-making and a results-motivated approach, while balancing opposing business priorities.
    • Strategic and Functional Problem Solving: Proficient analytical and critical thinking skills with the ability to solve complex problems at both strategic and operational levels.
    • Judgment and Business Acumen: Proven ability to exercise sound judgment in dynamic environments, aligning decisions with organizational goals and stakeholder expectations.
    • Leadership and Team Development: Demonstrated leadership in managing staff and achieving results through others, fostering a high-performance culture.
    • Crisis and Pressure Management: Proficient problem-solving abilities and the capacity to make effective decisions under pressure.
This position will fundamentally transform how employees interact with technology—ensuring that every digital touchpoint enhances productivity, fosters collaboration, and empowers teammates to do their best work seamlessly and securely. This role leads the vision, strategy, and execution of a modern digital workplace, with a clear focus on delivering a frictionless, intuitive, and resilient user experience.

At its core, this position is about enabling people through technology. By designing and delivering integrated digital solutions—spanning on-premise, cloud, and SaaS environments—this leader ensures that the workforce has the tools they need to thrive in a dynamic, hybrid work environment. The role partners closely with functional leaders to co-create experience roadmaps that not only meet today's needs but also anticipate and adopt emerging technologies that shape the future of work.

Salary.com Estimation for Senior Director, Digital Workplace Experience in Chicago, IL
$168,488 to $209,172
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